Tetrahydrofuran → (2-(1-Methyl-2-pyrrolyl)-6-benzoxazolyl)acetic acid

HRID 1372749Notes

Reaction equation

HRID 1372749 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[O:8][C:9]2[CH:15]=[C:14]([CH2:16][C:17]([O:19]C)=[O:18])[CH:13]=[CH:12][C:10]=2[N:11]=1.C1COCC1.[OH-].[Na+]>Cl>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[O:8][C:9]2[CH:15]=[C:14]([CH2:16][C:17]([OH:19])=[O:18])[CH:13]=[CH:12][C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58778961Methyl (2-(1-methyl-2-pyrrolyl)-6-benzoxazolyl)acetate

Product 1

HCID 17859194(2-(1-Methyl-2-pyrrolyl)-6-benzoxazolyl)acetic acidYield 67%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To methyl (2-(1-methyl-2-pyrrolyl)-6-benzoxazolyl)acetate (228 mg, 0.84 mmol) were added THF (8.5 ml) and 0.25N NaOH (5.10 ml, 1.27 mmol). The resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was poured in 1N HCl (10 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water, and dried under reduced pressure to give (2-(1-methyl-2-pyrrolyl)-6-benzoxazolyl)acetic acid (144 mg, 67%) as a pale yellow solid.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-85894485c3014132be685debbaceb52c
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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